Two seemingly unrelated news items from the last month: The tunnel boring machine digging the extension of the number 7 subway line completed its task, leaving the new project on target for a late 2013 opening. And the Downtown Brooklyn Partnership, a quasi-public development corporation formed to oversee the reconstruction of a 22-block swath of downtown Brooklyn, was reported to be short of cash and threatened with being reduced to "a shell" of its former self.

The tie that binds these two stories: Dan Doctoroff, who as deputy mayor for economic development spearheaded both the 7 train extension and the downtown Brooklyn rezoning, along with numerous other development projects that marked Mayor Bloomberg's first two terms in office. Initially brought in to oversee development tied to Bloomberg's ultimately fruitless bid for the 2012 Olympics—Doctoroff's previous job was as director of the city's Olympic bid committee, NYC2012—the former investment banker became a familiar visage on the city scene, with his Albert Brooks grin and ubiquitous Powerpoint presentations. ("You use Powerpoint the way Picasso used a brush," then-Councilmember Eric Gioia once enthused at a City Council hearing.)

It's been almost three years now since Doctoroff departed city government for the top job at Bloomberg LLC. In that time, both the city's finances and its real estate have entered uncertain waters, but the projects set in motion during Doctoroff's time at the helm continue to shape the city's future. Here's a look at some of Doctoroff's most notable projects, and how his development legacy—and Bloomberg's—look now.

  • Hudson Yards
    The Plan: Doctoroff first concocted plans for a redevelopment of the airspace above and land surrounding the rail yards west of Penn Station in 1999, when he was still running NYC2012. The plan for a combined Jets and Olympic stadium fell apart after state Assembly Speaker Sheldon Silver, using his veto power as a member of the Public Authorities Control Board, blocked it in June 2005. But rezoning of the site lived on, as did a city-funded $2.1 billion project to extend the 7 train to 33rd Street and 11th Avenue.

    What Happened: The 7 extension is on schedule to open in 2013, but for now it will still lead riders to a giant hole in the ground because the above-ground redevelopment is in limbo. After several years of disarray—original anchor tenants Morgan Stanley and Goldman Sachs both dropped out—this May the Related Companies, run by Doctoroff's old real estate business partner Stephen Ross, signed a 99-year lease with the MTA for the 26-acre railyard site for $1 billion, though it won't have to pay up (or begin construction) until the real estate market improves. (Running the project for Ross: Jay Cross, formerly in charge of the Jets' stadium push.) The city, meanwhile, has run through most of the payments by real estate developers slated to pay for the subway line and other infrastructure, and is facing nearly $100 million a year in debt payments on the project starting in 2011.

    Glass-Half-Full View: "I'm banking on the fact that the stars are finally aligned. ... It's possible for us to start at the beginning of 2012 or late 2011. ... We're sort of coming out of hibernation." -Jay Cross, president of Related Hudson Yards

    Glass-Half-Empty View: "What's to say the community wouldn't have developed in a saner way, with 15- to 20-story buildings, on its own? I'm looking at three [residential] buildings on 8th Avenue right out my window, and they're all empty." -John Fisher, West Side community activist

  • The Stadiums
    The Plan: Within a week of the Hudson Yards stadium plan's demise, Bloomberg announced he'd build two new baseball stadiums instead, one of which could be adapted for the Olympics. New York's Olympic bid was soon rejected by the IOC, but the plan to replace Yankee and Shea stadiums moved ahead, utilizing a complicated tax dodge concocted by Doctoroff for the Jets deal to help with the financing. While the Mets stadium was to built in the old Shea Stadium parking lot, the 28-acre Macombs Dam Park would be largely demolished to make way for the new Yankees stadium.

    What Happened: Despite community opposition, including a negative vote of the local community board, the Yankees stadium was approved in April 2006, as was the Mets project a few weeks later. The two stadiums opened in 2009, to mixed reviews.

    Glass-Half-Empty View: "It still looks as if it will be another full year before any [ballfields] are built and available for use by the community. My school's team is still playing their 'home games' as far away as Staten Island. However, after much arm-twisting, the organization sprang for a bus to help transport the teams. The much-touted economic development doesn't seem to have borne much fruit." -Joyce Hogi, Bronx community activist and Community Board 4 parks committee volunteer

    Glass-Half-Full View: “As promised, we completed the demolition of the old stadium in June, safely and on-budget. Upon completion [of Heritage Field, one of the replacement parks], the people of the South Bronx will not only have a new state-of-the-art Yankee Stadium that has created thousands of jobs for area residents, but a new Metro-North station, upgraded infrastructure and more than 32-acres of vastly improved and expanded parkland.” - NYCEDC President Seth Pinsky

  • Bronx Terminal Market
    The Plan: The city would take over and demolish the privately managed 1935-built market buildings just south of Yankee Stadium, turning the site's lease over to Ross's Related Companies for the construction of a shopping mall dubbed the Gateway Center. As part of the no-bid deal, Related would also receive $134 million in city tax breaks.

    What Happened: Despite protests by merchants, the Gateway project was approved in 2006 and the old market buildings demolished shortly thereafter. The mall, an imposing structure so geared to drawing drivers from the suburbs that pedestrian visitors must walk alongside parking ramps to enter, opened last year, and Home Depot, Target, and other major retailers took up tenancy. Many storefronts inside the mall remain empty; the city says the mall is nearing full occupancy.

    Glass-Half-Full View: "It has created hundreds of permanent, local jobs. It's generating revenue for the City. And it's making life a little easier for residents who no longer need to leave the borough to shop." -David Lombino, spokesperson, NYC Economic Development Corporation

    Glass-Half-Empty View: "Everything that's promised in the community benefits agreement, there's an exit for Related to get out of it. You don't have the opportunities that the community expected, and there's not the type of monitoring that benefits the tenants and benefits the community." -Greg Bell, Insight For New Housing

  • Downtown Brooklyn
    The Plan: Rezone 22 blocks of downtown Brooklyn to make it into a new commercial district. 'In the last boom, this city did not have the space for companies who wanted to stay here or relocate here," said Doctoroff in 2003. "We're still feeling the pain of that.' Spearheading the push: the Downtown Brooklyn Partnership, a private non-profit headed by Joe Chan, Doctoroff's former top aide at City Hall.

    What Happened: The office buildings never arrived, though some condo towers did, along with the Brooklyner, a 51-story rental building that is now the borough's tallest structure. The Albee Square Mall was razed for a never-built, mixed-use skyscraper, and now will be the site of a new four-story shopping mall; the planned "Willoughby West" mixed-use building around the corner, meanwhile, has yet to materialize, three years after the shopkeepers on its proposed site were evicted.

    Glass-Half-Empty View: "The downtown Brooklyn plan, which promised about 800 affordable units of housing, still hasn't kept that promise. They promised it would provide thousands of office jobs. Instead, it's nothing but condominiums that are going up. And all you get from that is temporary construction jobs and a few service jobs." -Valery Jean, director of Families United for Racial and Economic Equality

    Glass-Half-Full View: "As residences continue to be built, it'll bring thousands and thousands of families into downtown Brooklyn to live. ... We have all the amenities that any major city in America wishes that they enjoyed." -Brooklyn Borough President Marty Markowitz

  • Williamsburg/Greenpoint rezoning
    The plan: After a raucous public debate, and over Doctoroff's objections, the city agreed to rezone much of these Brooklyn neighborhoods to incorporate "inclusionary zoning," which allows taller residential buildings if developers set aside more units for affordable housing.

    What happened: After the rezoning, condo towers indeed began to sprout along the waterfront, though the collapse of the housing bubble left many of them largely empty. At the same time, even more development has taken place just outside the rezoned district, taking advantage of the neighborhood's rising property values without having to submit to the affordable housing requirements. Last month, the city council approved a 2,200-unit apartment complex on the site of the former Domino Sugar factory, with promises but no firm guarantees that affordable housing will be in the mix.

    Glass-Half-Full View: "Through rezoning this tract of long underused waterfront, we created powerful incentives that harness the real estate market and take advantage of the opportunity to maximize development while doing a world of good in this growing community." - Housing Preservation and Development Commissioner Rafael Cestero

    Glass-Half-Empty View: "It promised a huge amount of affordable housing, open space, infrastructure needs, reviews of schools, public safety, all the things you read about now that aren't happening here five years later. They can make a press release that looks really nice, but when the construction crews leave, then you've got to live with the results." -Phil DePaolo, New York Community Council